Azo dye



sures :GO @ELDEBHLANN FELIX MEYER, 9F DESSAU, ANHALT, GERMANY,

Tel? .QCTIEN GkEELISCHAFT FfTR ANILIN FABRIKATION, OF BERLIN, GER

PATENT OFFICE.

ASSIGNORS AZO DYE.

call w from it may co-zwern.

1 Be it known that we, Hcco (IELDERMANN and if i-Lnix Iilrricmpitizens ofthe Republico'f "Germany, residing at Dessau, in Anhult, have Iinvented certain new and eisetul improvements in Azo Dyes, (for' have made application in Germany ddivutive of diasotized fB-aminophenol and enzoylamino-T-oxynuphthalene a by heating molecular proportions Lem no-T-oxynuphtliuleue with phthulic iydride in low-boiling indifferentsolvents sue-n as benzene. They correspond to the Ltenerul formula no 11,, \W

"o substituents such as a nitro group or an ulkyl esc new dyes when dyed in the presence an alkali-metal chi-ornate and an ummonh um suit such as ammonium sulfate furnish vvocl olive tints of an excellent fastness to mi 5;.

in the shape of their dry pulveri: in so-F'uu: suits are dark powders soluble in water with 23, violet color and soluble in concentrated sulfuric acid to bluish red solutions from which on'additioii of ice the dye is precipitated in. the form oi reddish flocks. 33y strong reducing agents they are dostroyed yielding u EZ-uminophenol substituted the nucleo and 1.2-carboxybenzoylunlino- 8'S.llliIlO-7-OXYX1ZiPl1tllfilQIlG.

ln order to illustrate how the new dyes may be manufactured, without hunting the invention, the following example is given irts being by eight: 1 i I i'oirumple: 1!"). l parts of l-nitro-Q-uuiinophenol are diuzo'tized inknown manner by Specification of Letters Patent. Patented plan 28 1922 Application filed August 15, 1921., Serial in. 492,491.

means of hydrochloric acid and sodium-nitrite. Then the diazo compound is added to a solution'of 31 parts of l.2-curboxybenzoylumiho-T-oxynaphthulene maintained alkaline by sodium carbonate. When the combination is complete the dye is salted out, drained and dried. Its constitution in the free state is expressed by the formula OH no Its reduction products are 2.4-'diuminophenol and 1.2-curboxybenzoylumino-8-amino-T-oxynuphthulene. 7

Similar dyes are produced if the 4-nitro-2- eminophenol is replaced in the equivalent proportions by another Q-animophenol derivative for instance by 4-chlo'ro-, iii-dichloro-, 4.6-dinitro-, 5-nitro-4-methyb; 5- nit1'0-4-chl0ro-, 4nitr0-(5-chloro, o-nitrolchloro-Q-umino-l-oxybenzene,

Having now described our invention and in What manner it may be performed What we claim is,-

1. The new azo dyes in the free state correspond to the general formula.

where R is u univulent radical exclusive of c the sulto group; in the shape of their pul-, verized dry sodlum salts being; (lurk powders soluble in water With a violet color and soluble in concentrated sulfuric acid to bluish red v agents yielding a Q-ermnophenol substituted in the nucleo and 1.2'-curboxybenzoylumino- 8-amin'o-7 -0xynaphtha1ene; dyeing W001 salt being a dark powder soluble in Wii'ildi olive in the presence of an alkali-metal chr0- with a violet @0101 and soiubie in eoncen 20 F mate and an ammonium salt. traced suifui'ic acid to e bluish red solution 2. The new azo dye in. the free state oorfrom whieh on addition. of iee the dye is pre- 5 responding to the formula clpitated 1n the form of reddish flocks; LG-

ing destroyed by strong reducing agents yielding 2.4-dian1inopheno1 and 12"cerboxy- 25 henzoylamino 8 amino T-QXyna hth-tflene; dyeing wool olive in the presence of en elkali-metal chi-ornate andan. ammonium saite In testimony whereof We afiix oursigiiztt-ures in presence of two Witnesses.

HUGO GELDERMANN. FELIX MEYER.

Witnesses CARL D HUYER, in the shape of its pulverized dry sodium ALFRED W. DONEYUER. 

